Introducing this spacious 4-bedroom, 1.5-bath ranch on an extra-wide fenced lot in the Chester Harbor community, just minutes from historic Chestertown. Offering comfortable single-level living, the home features a large family room, an expansive kitchen with abundant cabinet and counter space, and a functional floor plan ready for your personal updates and vision. Whether youre looking for your next home, an investment opportunity, or a property to renovate and build equity, this home offers exceptional potential. The generous layout includes four bedrooms, one full bath, one half bath, and flexible space for guests, a home office, or hobbies. Outside, the oversized iron-fenced yard provides plenty of room for gardening, entertaining, pets, or future expansion. Enjoy your morning coffee or evening unwind on the side porch, while the attached one-car garage adds convenient storage. As part of the Chester Harbor community, youll enjoy access to the community boat ramp and the Chester River, making it easy to spend your days boating, fishing, kayaking, or simply enjoying life on the water. Ideally located near marinas, parks, and the shops, restaurants, and waterfront charm of historic downtown Chestertown, this property offers the perfect blend of space, convenience, recreation, and opportunity. Priced to reflect its condition, this is a chance to create a home thats uniquely your own while building equity in a sought-after location.
- MD
- Chestertown
- 21620
- 533 Round Top Rd
- MLS# MDQA2018038
- Date Listed07/19/2026
- Days on Realty 28 Days
- Bedrooms 4
- Bathrooms 1 Full baths, 1 Half baths
- Lot Size 0.55 acres (24,000 sq. ft)
- Subdivision CHESTER HARBOR
- Year Built 1962
- Square Feet 1,800 sq. ft
- Price Per Sq. Ft $125
Interior Features
- Cooling None
- Heating Forced Air
Exterior / Lot Features
- Roof -
- Lot Size Acres 0.55
- Lot Size SQFT 24,000.00
- Lot Features -
Financial Considerations
- Tax Amount $2,144
- Terms Cash, Conventional, FHA, VA Loan
Schools near 21620
Explore the local neighborhood highlights and top-rated schools near 21620 in Chestertown, MD.
Nearby Schools
Source: School Digger
Public • PK - 5 • Serves this home
26.4 mi
Distance
Public • 3 - 5 • Serves this home
16.17 mi
Distance
Queen Anne's County High School
Public • 9 - 12 • Serves this home
16.17 mi
Distance
Public • PK - 5 • Serves this home
26.4 mi
Distance
Public • PK - 2
29.95 mi
Distance
Public • PK - 5
32.35 mi
Distance
Public • 3 - 5 • Serves this home
16.17 mi
Distance
Public • 6 - 8
17.04 mi
Distance
Public • 6 - 8
29.95 mi
Distance
Public • 3 - 5
29.95 mi
Distance
Public • 6 - 8
32.86 mi
Distance
Queen Anne's County High School
Public • 9 - 12 • Serves this home
16.17 mi
Distance
Public • 9 - 12
29.26 mi
Distance
Sales & Tax History
Source: Public Records
| Street Address | Beds | Baths | Sold Date | List Price | Valuation Date | Valuation Price |
|---|---|---|---|---|---|---|
| 129 Trafford Dr | 3 | 3 | Aug 10, 2026 | $314,900 | Aug 16, 2026 | - |
| 118 Grant Ct | Listing | 3 | 2 | Jun 29, 2026 | $305,350 | Mar 21, 2024 | $400,018 |
| 301 HICKORY LN,CHESTERTOWN,MD,21620,QUEEN ANNES | Listing | 4 | 3 | Jul 16, 2026 | $650,000 | Dec 28, 2020 | $624,000 |
| 115 Chester Arms Dr | Listing | 3 | 2 | Aug 15, 2026 | $238,000 | Dec 28, 2020 | $177,000 |
| 100 WAYNE ST,SUDLERSVILLE,MD,21668,QUEEN ANNES | Listing | 3 | 1 | Jul 10, 2026 | $209,900 | Mar 21, 2024 | $214,707 |
| 611 Cannon St | Listing | 2 | 2 | Jun 27, 2026 | $240,000 | Mar 21, 2024 | $223,867 |
| 306 Roosevelt Dr | 3 | 2 | Jun 19, 2026 | $250,000 | Aug 16, 2026 | - |
| 27719 Lambs Meadow Rd | Listing | 3 | 2 | Jun 19, 2026 | $475,000 | Jul 23, 2024 | $312,243 |
| 25087 Reeds Meadow Dr | 3 | 2 | Jun 19, 2026 | $339,900 | Aug 16, 2026 | - |
| Lot 4 FINLEY CREEK DR,CENTREVILLE,MD,21617,QUEEN ANNES | 3 | 3 | Jul 16, 2026 | $1,053,900 | Aug 16, 2026 | - |
Local Neighborhood Highlights for 21620
Discover key demographics, population statistics, and environmental insights for the Chestertown, MD area.
Population & Environment
Source: Sperling's Best Places
| Zip | City | County | National | |
|---|---|---|---|---|
| Population | 13,642 | 5,474 | 20,592 | 335,858,263 |
| Population Density | 115 | 2,026 | 74 | 95 |
| People per Household | 2.3 | 2 | 2.3 | 2.6 |
| Median Age | 41 | 33.3 | 44.3 | 39.1 |
| Median Income | $64,498 | $50,694 | $61,161 | $66,222 |
| Average Income | $36,801 | $31,193 | $36,819 | $35,475 |
| Cost of Living Index | 85 | 72 | 86 | 100 |
| Zip | City | County | National | |
|---|---|---|---|---|
| January Avg. High Temp | 24.8°F | 24.8°F | 24.8°F | 22.6°F |
| July Avg. High Temp | 87.8°F | 87.8°F | 87.8°F | 86.2°F |
| Annual Precipitation | 44.84" | 44.84" | 44.84" | 38" |
1/100
Car-Dependent
Walk Score ®
0/100
Minimal Transit
Transit Score ®
29/100
Bikable
Bike Score ®
Overview
Almost all errands require a car. It is possible to get on a bus. Minimal bike infrastructure.
Walkability averages in the surrounding area
The average walkability score in the surrounding area is Walk Score: 8/100, Transit Score: 0/100, Bike Score: 28/100.
Property Change History
Points of Interest near 533 Round Top Rd, Chestertown, MD 21620
0.43 mi
Distance
1.11 mi
Distance
1.17 mi
Distance
0.74 mi
Distance
1.28 mi
Distance
1.44 mi
Distance
0.88 mi
Distance
1.09 mi
Distance
1.44 mi
Distance
0.83 mi
Distance
0.83 mi
Distance
1.02 mi
Distance
0.6 mi
Distance
0.72 mi
Distance
0.9 mi
Distance
0.99 mi
Distance
1.63 mi
Distance
1.65 mi
Distance
1.71 mi
Distance
1.72 mi
Distance
1.74 mi
Distance
Nearby Properties
-
$210,000 Active Under Contract3 bds • 2 ba • 1,863 sqft
3701 Barclay Rd, Marydel, MD 21649
Welcome to 3701 Barclay Rd, a fantastic opportunity to own a 3-bedroom, 2-bath manufactured home on nearly half an acre in the peaceful countryside of Queen Anne's County. Built in 2004, this property offers a spacious open floor plan ready for your...Listing by: Elizabeth Keyser - LPT Realty, LLC -
New$239,000 Active4 bds • 1 ba • 1,618 sqft
3399 Hartly Rd, Hartly, DE 19953
Location, Location, Location! Positioned at the prominent intersection of Hartly Road and Halltown Road, this nearly 2-acre property presents a compelling opportunity for investors, entrepreneurs, and owner-users seeking visibility, accessibility, an...Listing by: Teri Freeman - Long & Foster Real Estate, Inc. -
$249,900 Active3 bds • 2 ba • 1,565 sqft
1024 Westshore Dr, Edgewood, MD 21040
NEW PRICE & INCREDIBLE VALUE BELOW $250K! Welcome to 1024 Westshore Drive, a beautifully maintained 3-bedroom, 2-bathroom townhome in Edgewood's desirable West Shore community. Step inside to find a spacious, light-filled main level that flows effort...Listing by: Stephanie R Handy - EXP Realty, LLC -
$258,000 Active3 bds • 3 ba • 1,574 sqft
704 Saint Peters Ct, Edgewood, MD 21040
OPEN HOUSE- SUNDAY 5/17 FROM 1PM-4PM Move-In-Ready! Beautiful & cozy brick-townhome featuring 3 bedrooms, 2.5 baths, freshly painted, new carpets in all bedrooms and new floorings throughout. Spacious kitchen with bay window. Fully finished walk out...Listing by: LINH Q HANG - Excel Realty Corp. -
$219,999 Active6 bds • 2 ba • 1,626 sqft
1886 Grempler Way, Edgewood, MD 21040
Step into modern comfort with this stunningly renovated 6-bedroom, 1.5-bathroom townhome on 1886 Grempler way. This home is fully upgraded and move-in ready, shines with designer finishes, fresh neutral paint, and sleek new flooring throughout a mix...Listing by: VELI S ALTAS - ExecuHome Realty -
$255,000 Active3 bds • 3 ba • 1,700 sqft
1670 Mohegan Dr #E, Havre De Grace, MD 21078
Excellent investment opportunity! Tenant occupied with lease in place through February 2027, providing immediate rental income. This 3-bedroom, 2.5-bath townhouse-style condo features an attached one-car garage and a functional floor plan. Residents...Listing by: Amy Dondero - Advance Realty USA INC -
$250,000 Active3 bds • 3 ba • 1,560 sqft
34 Helmsman Ct, Essex, MD 21221
Sellers ready to move on and give you the opportunity for this 3-bedroom home tucked away in a quiet, nature-filled setting with calming water views. This inviting residence offers one full bath and two half baths, blending comfort and convenience ac...Listing by: David E Straitman - EXP Realty, LLC -
$229,000 Active3 bds • 2 ba • 1,552 sqft
1021 Foxchase Ln, Essex, MD 21221
Very nice 3 bedroom/2 bath interior Townhome convenient to 702/695/95 awaits you! Inside the home, Owners sanded and restrained wooden floor, replaced upstairs bathroom shower walls, installed a new ceiling step ladder, replaced basement utility...Listing by: Maksim Liskovich - R&R Executive Realty -
New$229,900 Active2 bds • 2 ba • 1,575 sqft
104 E Main St, Middletown, DE 19709
Welcome to 104 E. Main Street, nestled in the heart of historic Middletown. This charming 2 bedroom, 1.5 bath home is a true gem, offering the perfect combination of timeless character and modern convenience. Thoughtfully updated, this home boasts re...Listing by: Robert Hoesterey - Crown Homes Real Estate -
$255,000 Active3 bds • 3 ba • 1,868 sqft
5 Cardinal Rd, Baltimore, MD 21221
Welcome to 5 Cardinal Road, a beautifully updated 3-bedroom, 2.5-bath brick townhome tucked away on a quiet cul-de-sac in Essex. Combining modern updates with timeless charm, this move-in-ready home offers three finished levels of comfortable living...Listing by: Luke C Skovira - Cummings & Co Realtors -
$250,000 Active3 bds • 1 ba • 1,870 sqft
7920 Charlesmont Rd, Dundalk, MD 21222
Welcome to 7920 Charlesmont Road, a thoughtfully updated home offering flexible living space, everyday convenience, and inviting areas to enjoy both indoors and out. The enclosed front porch creates a comfortable setting for morning coffee, reading,...Listing by: Samantha Boone - Keller Williams Flagship -
$250,000 Active Under Contract3 bds • 3 ba • 1,960 sqft
813 Thimbleberry Rd #813, Baltimore, MD 21220
Welcome to 813 Thimbleberry Road in Chestnut Woods! This well-maintained brick townhome offers 3 bedrooms, 2.5 baths, and three levels of comfortable living space. Gleaming hardwood floors flow throughout the main level, leading to a recently updated...Listing by: Natalie W Frazier - United Real Estate Executives -
$255,000 Active Under Contract3 bds • 3 ba • 1,734 sqft
404 Worchester Dr, Dover, DE 19904
Back on the market at no fault of the sellers. Charming home looking for a new owner. Nestled in the Village of Westover, this diamond in the rough twin home offers a perfect blend of comfort and convenience, making it an ideal retreat for those seek...Listing by: Sandra Miller - Long & Foster Real Estate, Inc. -
$235,000 Active3 bds • 3 ba • 1,693 sqft
1204 Blue Heron Dr, Denton, MD 21629
***NEWLY ADJUSTED PRICE***Come on in to explore this beautifully maintained 3-level home offering the perfect blend of modern convenience and comfortable living. This beauty features 3 spacious bedrooms and 2.5 baths, with an open floor plan that cre...Listing by: Carolyn Page - Shore Results Realty -
$225,000 Active3 bds • 3 ba • 1,730 sqft
6 Chase Hall, Dover, DE 19904
Nestled in the charming English Village, this inviting 3 bedroom, 2.5 bathroom unit offers a perfect blend of comfort and functionality. The traditional floor plan features a spacious combination dining and living area, ideal for gatherings and cozy...Listing by: LaSonya S. Snead - Coldwell Banker Premier - Rehoboth -
$240,000 Active4 bds • 1 ba • 1,860 sqft
119 Sollers Point, Baltimore, MD 21222
Spacious Colonial in Popular Turner Station - Investor Opportunity Bring your vision to this large Colonial home situated on a flat, conveniently located lot in sought-after Turner Station. The home offers four generously sized bedrooms and a shared...Listing by: Anne Parks - American Premier Realty, LLC -
$200,000 Active4 bds • 2 ba • 1,904 sqft
2922 Sollers Point Rd, Baltimore, MD 21222
Rare opportunity to own a remodeled, ready-to-be-rented income-producing duplex townhome in a convenient Dundalk location! This versatile property features two separate residential units, each with its own electric meter, making it an excellent inves...Listing by: Eric G. Chamish - Black Dog Realty, LLC -
$200,000 Active0 bds • 0 ba • 1,904 sqft
2922 Sollers Point Rd, Baltimore, MD 21222
Rare opportunity to own a remodeled, ready-to-be-rented income-producing duplex townhome in a convenient Dundalk location! This versatile property features two separate residential units, each with its own electric meter, making it an excellent inves...Listing by: Eric G. Chamish - Black Dog Realty, LLC -
$209,900 Active3 bds • 2 ba • 1,536 sqft
856 Jeannette Ave, Baltimore, MD 21222
Beautiful 3 bed 1.5 bath rowhome with a finished basement, gorgeous hardwood floors on the main and upper levels. Open concept kitchen area with stainless steel, beautiful maple cabinets and granite countertops. Rear covered deck, open back yard that...Listing by: Edward F Doonan Jr. - Samson Properties -
$215,000 Active2 bds • 2 ba • 1,570 sqft
32 Cox Ln #40, Camden, DE 19934
This stunning Saratoga model home has been thoughtfully updated, meticulously maintained, and is located in the sought-after 55+ active adult community of Barclay Farms. The beautifully appointed kitchen features crisp white Amish-built custom cabine...Listing by: Susan A Fitzwater - RE/MAX Advantage Realty
Similar Priced Comparison
-
$200,000 Active1 bds • 1 ba • 700 sqft
117 Water St N #1b
- Home smaller by 1,100 sqft
- Lot smaller by 24,000 sqft
- Older by 77 years
Listing by: Liddy Campbell - TTR Sotheby's International Realty -
$205,000 Active Under Contract3 bds • 1 ba • 1341 sqft
202 Pine St
- Home smaller by 459 sqft
- Lot smaller by 11,400 sqft
- Older by 7 years
Listing by: Jyaire T McCall - Coldwell Banker Chesapeake Real Estate Company -
$264,900 Active3 bds • 2 ba • sqft
121 Metcalf Rd
- Home smaller by 1,800 sqft
- Lot smaller by 20,080 sqft
- Newer by 63 years
Listing by: David J. Moore - Real Broker, LLC - Chester -
$275,000 Active Under Contract2 bds • 2 ba • 920 sqft
611 Cannon St
- Home smaller by 880 sqft
- Lot smaller by 18,135 sqft
- Newer by 18 years
Listing by: Hayley A Norris - Select Land & Homes, LLC -
$259,900 Active3 bds • 2 ba • 1280 sqft
115 Metcalf Rd
- Home smaller by 520 sqft
- Lot smaller by 21,760 sqft
- Newer by 63 years
Listing by: David J. Moore - Real Broker, LLC - Chester -
$240,000 Active Under Contract3 bds • 1 ba • 1140 sqft
107 Conley Dr
- Home smaller by 660 sqft
- Lot smaller by 19,700 sqft
- Newer by 24 years
Listing by: Taylor Leaverton - Benson & Mangold, LLC -
$239,900 Active3 bds • 2 ba • 1280 sqft
104 Conley Dr
- Home smaller by 520 sqft
- Lot smaller by 21,000 sqft
- Newer by 17 years
Listing by: Heather Kooser - Cummings & Co. Realtors -
$275,000 Active3 bds • 3 ba • 1900 sqft
104 Acorn Dr
- Home larger by 100 sqft
- Lot smaller by 21,881 sqft
- Newer by 42 years
Listing by: Sarah E. King - Cross Street Realtors LLC -
$275,000 Active3 bds • 1 ba • 1248 sqft
956 Washington Ave
- Home smaller by 552 sqft
- Lot larger by 6,000 sqft
- Newer by 13 years
Listing by: Grace M Crockett - Doug Ashley Realtors, LLC
Nearby Locations
Communities
- Historic Chestertown Homes For Sale
- Chester River Landing Homes For Sale
- North Brook Homes For Sale
- Symphony Village at Centreville Homes For Sale
- Indian Acres Homes For Sale
- Braemar Homes For Sale
- Hillside Homes For Sale
- Queens Landing Homes For Sale
- Bulle Rock Homes For Sale
- Holly Woods Homes For Sale
- Ellendale Homes For Sale
- Magnolia Landing Homes For Sale
- Harford Village Homes For Sale
- Bowleys Quarters Homes For Sale
- Joppatowne Homes For Sale
- Constant Friendship Homes For Sale
- Williams Estates Homes For Sale
- Chesapeake Easton Club East Homes For Sale
- Queen Anne Colony Homes For Sale
- Greenbrier Hills Homes For Sale
Nearby Zips
- 21620 Homes For Sale
- 21678 Homes For Sale
- 21651 Homes For Sale
- 21617 Homes For Sale
- 21635 Homes For Sale
- 21919 Homes For Sale
- 21661 Homes For Sale
- 21660 Homes For Sale
- 21658 Homes For Sale
- 19938 Homes For Sale
- 19953 Homes For Sale
- 21639 Homes For Sale
- 21638 Homes For Sale
- 21915 Homes For Sale
- 21040 Homes For Sale
- 21001 Homes For Sale
- 21619 Homes For Sale
- 21903 Homes For Sale
- 21629 Homes For Sale
- 19934 Homes For Sale
Nearby Cities
- Kingstown, MD Homes for Sale
- Church Hill, MD Homes for Sale
- Chestertown, MD Homes for Sale
- Pomona, MD Homes for Sale
- Worton, MD Homes for Sale
- Centreville, MD Homes for Sale
- Millington, MD Homes for Sale
- Galena, MD Homes for Sale
- Earleville, MD Homes for Sale
- Rock Hall, MD Homes for Sale
- Queenstown, MD Homes for Sale
- Ridgely, MD Homes for Sale
- Hartly, DE Homes for Sale
- Greensboro, MD Homes for Sale
- Grasonville, MD Homes for Sale
- Kent Narrows, MD Homes for Sale
- Bush River, MD Homes for Sale
- Aberdeen, MD Homes for Sale
- Townsend, DE Homes for Sale
- Chester, MD Homes for Sale
Similar Searches
- Chestertown Land for Sale
- Chestertown New Homes for Sale
- Chestertown Single Story Homes for Sale
- Chestertown Homes with Pools for Sale
- Chestertown Cheap Homes for Sale
- Chestertown Luxury Homes for Sale
- Chestertown Condos for Sale
- Chestertown Town Homes for Sale
- Chestertown Commercial for Sale
- Chestertown Open Houses for Sale
- Chestertown Two Car Garage Homes for Sale
- Chestertown Large Lots for Sale
- National Listings
- National Home Values
- Properties in MD
- Home Values in MD
- Home Values in Chestertown, MD
Frequently Asked Questions for 533 Round Top Rd
Source: Realty.com
533 Round Top Rd, Chestertown, MD 21620 in CHESTER HARBOR, Chestertown, MD 21620 is a single family listed at $225,000. Highlights include 4 bedrooms, 2 bathrooms, 1,800 sq. ft., built in 1962, 0.55 acre lot, $125 per sq. ft.. Realty.com has 1 photos, sales history, school insights, and mortgage tools for this listing.
Our records indicate that 533 Round Top Rd was built in 1962.
The full address for this home is 533 Round Top Rd, Chestertown, MD 21620.
533 Round Top Rd has been listed on Realty.com since Sun July 19, 2026
Almost all errands require a car. It is possible to get on a bus. Minimal bike infrastructure.
The average walkability score in the surrounding area is Walk Score: 8/100, Transit Score: 0/100, Bike Score: 28/100.
There are 3 schools assigned to this home. Check out the schools near 533 Round Top Rd. Grasonville Elementary School (Grades: PK - 5), Kennard Elementary School (Grades: 3 - 5), Queen Anne's County High School (Grades: 9 - 12)
Listing provided courtesy of:
Exp Realty, Llc
(tel: 833-335-7433)
Listing agent:
Christopher Craddock
(tel: 703-995-0333)
(#3049573)
This content last refreshed on 2026-08-16 22:06:13. Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.